Acetic Acid → HCID 86649970, compound

HRID 1042499Notes

Reaction equation

HRID 1042499 reaction equation
[CH3:1][O:2][N:3]([CH3:14])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[NH2:12].[CH3:15][C:16](O)=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:20].[Na+]>ClCCl>[CH3:1][O:2][N:3]([CH3:14])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[NH:12][CH2:19][CH2:20][CH2:16][CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 63110530HCID 63110530, compound

Product 1

HCID 86649970HCID 86649970, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-amino-4-fluorobenzoic acid amide (0.35 g, 1.75 mmol), butyrylaldehyde (0.23 mL, 2.62 mmol), and AcOH (0.15 mL, 2.62 mmol) in dichloromethane (20 mL) was added sodium triacetoxyborohydride (0.74 g, 3.49 mmol) at 5° C. The mixture was stirred for 5 hours at the same temperature and overnight at room temperature. The reaction was quenched by adding water. The organic layer was washed with saturated aqueous NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound quantitatively.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. washThe organic layer was washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d9200d2d06a46d39e25fcdd02a04886
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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